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Trifluoroacetic acid → HCID 59577332, compound

HRID 1526043
Notes
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Reaction equation

HRID 1526043 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[C:45]([F:47])[CH:46]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:31][CH2:32][CH:33]1[CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]1)=[O:17].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:35]1[CH2:34][CH:33]([CH2:32][NH:31][C:19]2[CH:20]=[C:21]([N:24]3[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]3)[CH:22]=[CH:23][C:18]=2[C:16]([NH:15][C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][C:4]4[CH:3]=[C:2]([F:1])[CH:46]=[C:45]([F:47])[CH:44]=4)[CH:7]=3)[NH:11][N:10]=2)=[O:17])[CH2:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68672281HCID 68672281, compound

Product 1

HCID 59577332HCID 59577332, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-butyl 3-({[2-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-5-(4-methylpiperazin-1-yl)phenyl]amino}methyl)azetidine-1-carboxylate (289 mg, 0.45 mmol) was dissolved in DCM (3 mL) and TFA (0.7 mL) was added. The resulting reaction solution was stirred overnight at room temperature. The mixture was diluted with DCM and extracted with 10% aqueous NH3. Organic phase was evaporated. Reverse phase column chromatography purification afforded 104 mg of the title compound.

Workup

  1. customThe resulting reaction solution
  2. extractionextracted with 10% aqueous NH3
  3. customOrganic phase was evaporated
  4. customReverse phase column chromatography purification

Sources & evidence

ORD record
ord-8a2a5f3dabe54235b5f87a6e0d1b3fb9
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085558B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes